I've spent a good amount of time reading through everyone's suggestions about better file management with the Media Library -- and at the end of the day, I haven't come across any clear winners at the moment. I saw this question/answer about adding taxonomies to the Media Library -- but it looks like that experience is an open text-field (not incredibly user friendly). Is that the best we'll get with that at the moment. What I would hope for is an experience just like any other taxonomy screen.

I've seen Custom Upload Directory which is falling pray to some PHP errors (so I can't properly test) and Media Categories which while nice -- doesn't satisfy the needs of adding the media itself. Here's a run-down of what I was looking for:

Allow categories in the Media Library (once a suitable UI solution is found -- that initial answer looks like it can then provide the ability to sort by a taxonomy

Add that same category selection-box to the media modal pop-up

Allow users to filter by a specific category (select or open-text field) based on a taxonomy

Automatically assign uploaded files a category either based on image-type or post-type

As I typed that it seems like it's more of a wishlist than a proper question to go on here -- but I have tried to do my due diligence in researching beforehand -- just not sure if this will be a clusterf*** of the possible solutions here. Any hints in the right direction? Thanks!